Season 5
19 episodes · Sep 24, 2007
Charlie finds himself in unfamiliar territory with real feelings, Alan keeps stumbling through relationships, and Jake edges from boyhood into teenage antics.
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S5E1Large Birds, Spiders and Mom
Sep 24, 200720mJake is getting ready to start a new school as he graduates to Junior High. Alan and Charlie take him school shopping and find themselves in trouble.
S5E2Media Room Slash Dungeon
Oct 1, 200722mCharlie acts strange after spending an evening with his mother, and a woman Alan slept with behaves oddly the next morning.
S5E3Dum Diddy Dum Diddy Doo
Oct 8, 200721mAlan convinces Charlie that he needs to date more respectable women and sets him up with a judge. The two double date and their waitress happens to be one of Charlie's ex-girlfriends. Charlie's date backfires the following morning, when he ends up in court in front of the judge.
S5E4City of Great Racks
Oct 15, 200722mCharlie and Linda get closer to consummating their relationship, but Charlie has trouble focusing when he begins to see Rose's face everywhere he turns.
S5E5Putting Swim Fins on a Cat
Oct 22, 200722mCharlie has to come up with ways to keep his girlfriend's 4-year-old amused; Alan becomes a test subject.
S5E6Help Daddy Find His Toenail
Oct 29, 200721mCharlie's girlfriend is embrassed to go out in public with him. Meanwhile, Jake sneaks out to attend a concert.
S5E7The Leather Gear Is in the Guest Room
Nov 5, 200720mAfter Alan and Charlie have a fight about Alan's role in the house. Alan packs Jake up and moves in with his mother.
S5E8Is There a Mrs. Waffles?
Nov 12, 200720mCharlie writes a children's song and finds success as Charlie Waffles. The children love him and the mothers seem to as well. Charlie's new found fame irritates Alan.
S5E9Shoes, Hats, Pickle Jar Lids
Nov 19, 200720mCharlie fights his attraction for Teddy's daughter.
S5E10Kinda Like Necrophilia
Nov 26, 200722mAlan finds out that Charlie stole his girlfriend and works on a plan to get back at Charlie, even though this happened when they were in high school.
S5E11Meander to Your Dander
Mar 17, 200822mWhen Alan finds himself wanting to break up with a woman, Charlie offers his expertise.
S5E12A Little Clammy and None Too Fresh
Mar 24, 200822mRose returns from England, and plays nurse rather oddly for an ill Charlie.
S5E13The Soil Is Moist
Mar 31, 200820mAlan finds out some surprising information about Judith's sex life when he decides to go on a date with one of her friends.
S5E14Winky-Dink Time
Apr 14, 200822mCharlie double-dates with Jake and fixes Alan up with a hooker.
S5E15Rough Night in Hump Junction
Apr 21, 200821mAlan feels Charlie is unable to control his womanizing ways.
S5E16Look at Me Mommy, I'm Pretty
Apr 28, 200822mAlan makes wedding plans for Evelyn and Teddy, while Charlie figures out how to get more acquainted with his future step-sister.
S5E18If My Hole Could Talk
May 12, 200821mCharlie's attracted to an older self-help author. Alan and Jake clash over a project for school.
S5E19Waiting for the Right Snapper
May 19, 200822mWhen Charlie meets Angie's soon to be daughter-in-law, he realizes it's not for the first time.